6-hepten-2-one oxime | 57606-77-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-hepten-2-one oxime
• 英文别名: hept-6-en-2-one oxime；N-hept-6-en-2-ylidenehydroxylamine
• CAS: 57606-77-6
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: PENSONVLXBZDFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hepten-2-one oxime 在 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 反应 27.0h， 生成 trans-Methyl 2-(3-Cyanopropyl)-6-methylpiperidine-1-carboxylate
  参考文献：
  名称：

  Adams, David R.; Carruthers, William; Williams, Michael J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 1507 - 1513

  摘要：

  DOI：
• 作为产物：
  描述：

  庚-6-烯-2-酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 6-hepten-2-one oxime
  参考文献：
  名称：

  立体选择性亲电试剂诱导的烯基肟O-烯丙基和O-苄基醚的单环和双环化-片段化反应。二氢吡啶的合成

  摘要：

  苯硒基溴诱导的γ-和δ-不饱和醛肟和酮肟O-烯丙基和O-苄基醚的环化反应，然后缓慢氧化所得的氧亚胺离子，得到环状亚胺盐，这些亚胺盐很容易被钠还原为吡咯烷，哌啶或四氢异喹啉硼氢化物 二烯基肟通过在汞（II）诱导的环化反应中终止的类似序列产生吲哚并咪唑和喹喔啉。

  DOI：

  10.1016/s0040-4020(01)01118-8

文献信息

• X=Y-ZH systems as potential 1,3-dipoles. Part 33. Generation of nitrones from oximes. Tandem Michael addition-1,3-dipolar cycloaddition reactions. Class 2 processes in which the dipolarophile is located within the oxime.
  作者：Paul Armstrong、Ronald Grigg、Frances Heaney、Sivagnanasundram Surendrakumar、William J Warnock

  DOI：10.1016/s0040-4020(01)87117-9

  日期：1991.1

  corresponding C-alkenyl nitrones which undergo an intramolecular cycloaddition. The cycloaddition can occur by one of two modes leading to either bridged- or fused-isoxazolidines. The latter is preferred in most cases except that of the C-(3-alkenyl) nitrone which gives exclusively the bridged-ring product and the C-(4-alkenyl)nitrones derived from N-allylpyrrole-2-carboxyaldehyde oxime which gives both bridged-

  C-3，-4，-5和-6-烯基肟通过迈克尔加成法或烯型方法与氮原子上的负电性烯烃反应，生成相应的C-烯基硝酮，并进行分子内环加成。环加成可以通过两种方式之一发生，从而导致桥联或稠合的异恶唑烷。在大多数情况下，后者是优选的，除了仅产生桥环产物的C-（3-烯基）硝酮和衍生自N-烯丙基吡咯-2-羧醛肟的C-（4-烯基）硝酮外。桥环和稠环异恶唑烷。
• Halogen-induced formation of nitrones from oximes and alkenes
  作者：Ronald Grigg、Maria Hadjisoteriou、Peter Kennewell、Jasothara Markandu、Mark Thornton-Pett

  DOI：10.1039/c39930001340

  日期：——

  Oximes possessing γ-, δ-, or ω-alkenyl substituents are cyclised by N-bromosuccinimide or iodine to the corresponding cyclic nitrones or their dimeric H-bonded hydriodide salts in good yield; facially specific cycloaddition of these nitrones, and others derived by cyclisation of a δ,δ-bis(alkenyl) ketoxime or addition of acetaldoxime to cyclohexene, furnish isoxazolidines.

  具有γ-、δ-或ω-烯基取代基的肟在 N-溴代琥珀酰亚胺或碘的作用下环化成相应的环状亚硝基膦或它们的二聚 H 键氢化物盐，收率很高；这些亚硝基膦以及其他通过环化δ,δ-双（烯基）酮肟或将乙醛肟加成到环己烯而得到的亚硝基膦的表面特异性环化反应生成异噁唑烷。
• XY–ZH Systems as potential 1,3-dipoles. Part 51: Halogen-induced inter- and intra-molecular formation of nitrones from oximes and alkenes
  作者：H Ali Dondas、Ronald Grigg、Maria Hadjisoteriou、Jasothara Markandu、Peter Kennewell、Mark Thornton-Pett

  DOI：10.1016/s0040-4020(00)01084-x

  日期：2001.2

  Oximes possessing γ- and δ-alkenyl substituents are cyclised by N-bromo- or N-iodosuccinimide, iodine or ICl to the corresponding cyclic nitrones or their dimeric H-bonded hydroiodide salts in good yield; facially specific cycloaddition of these nitrones, and others derived by cyclisation of δ,δ-bis(alkenyl) ketoximes or by iodine induced addition of acetaldoxime to cyclohexene, furnish isoxazolidines

  用N-溴代或N-碘代琥珀酰亚胺，碘或ICl将具有γ-和δ-烯基取代基的肟环化成相应的环状硝酮或其二聚体H键合的氢碘化物盐；这些硝酮的表面特定的环加成，以及其他由δ，δ-双（烯基）酮肟环化或碘诱导的乙醛肟向环己烯的加成反应而提供的异恶唑烷。
• Phenylselenyl halide induced formation of cyclic nitrones from alkenyl oximes
  作者：Ronald Grigg、Maria Hadjisoteriou、Peter Kennewell、Jasothara Markandu

  DOI：10.1039/c39920001537

  日期：——

  Oximes possessing alk-γ- or -δ-enyl substituents are cyclised by phenylselenyl bromide, or by phenylselenyl chloride and an appropriate silver salt, to the corresponding cyclic nitrones; the seleno nitrones undergo facially specific cycloadditions with N-methylmaleimide, bis(alk-γ,δ-enyl) and bis(alk-δ,δ-enyl) ketones undergo regiospecific cyclisation and stereospecific cycloaddition to furnish spirocyclic

  具有烷基-γ-或-δ-烯基取代基的肟被苯基硒烯基溴化物或苯基硒烯基氯和适当的银盐环化成相应的环状硝酮；硒代硝基酮与N-甲基马来酰亚胺，双（alk-γ，δ-烯基）和双（alk-δ，δ-烯基）酮进行表面特异性环加成反应，进行区域特异性环化和立体有规环加成反应，提供螺环产物。
• XY–ZH Systems as Potential 1,3-Dipoles. Part 50: Phenylselenyl Halide Induced Formation of Cyclic Nitrones from Alkenyl Oximes
  作者：H.Ali Dondas、Ronald Grigg、Maria Hadjisoteriou、Jasothara Markandu、W.Anthony Thomas、Peter Kennewell

  DOI：10.1016/s0040-4020(00)01012-7

  日期：2000.12

  Oximes possessing γ-, δ or ω-alkenyl substituents are cyclised by phenylselenyl bromide, or by phenylselenyl chloride and an appropriate silver salt to the corresponding cyclic nitrones; the seleno nitrones undergo facially specific cycloaddition reactions with N-methylmaleimide; bis(alk-γ,δ-enyl) ketones undergo regiospecific cyclisation and stereospecific intramolecular cycloaddition to furnish spirocyclic

  具有γ-，δ或ω-烯基取代基的肟被苯基硒烯基溴化物或苯基硒烯基氯和适当的银盐环化成相应的环状硝酮；硒代硝基酮与N-甲基马来酰亚胺发生表面特定的环加成反应；双（alk-γ，δ-烯基）酮经过区域特异性环化和立体特异性分子内环加成反应提供螺环产物。